The Pink Side (transgender-tv)
By Gingerfred Man
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Chapter One – Selected
It's usually not good to be the new kid in school. Especially not in high school. And super especially not your senior year in high school.
Unless you're someone like Tiffany Gusher.
As if there were others like Tiffany Gusher.
Tiffany slithered into our English class on the first day of her and my senior year like someone in charge of all she surveyed.
And she was quite a surveyor.
Her facial beauty was stunning enough. But the way she dressed...
Oooh la la!
The other girls in school apparently bought their clothes by the pound. From the pile that any self-respecting ragman would have rejected.
Tiffany dressed like a woman.
Maybe not a 21st Century woman. More like a mid-1950s woman.
Thus, oooh la la!
She wore tan, seamed, fully-fashioned, reinforced-heel-and-toe stockings; a yellow mini-sundress that exposed her magnificent shoulders and her endless legs; and stratospheric, yellow, strappy heels.
All 13 male heads turned when Tiffany entered the classroom, including the English teacher, Mr. Chaucer.
The 11 other "girls" in the class looked at her with a mixture of loathing, hate, wild surmise, and a wisp of envy.
Which was apparently exactly the reaction Tiffany wanted.
She settled into her seat, being careful to allow the truly attentive a brief glance at her stocking tops, then appeared to be all about the business of learning.
I admit that I stole a glance or two at Tiffany during class. I'm pretty sure that I saw a film of cold sweat on Mr. Chaucer's upper lip as he described the upcoming semester. And stole his own glances every time Tiffany crossed and uncrossed those amazing legs.
After class, I heard one of the girls (I think it was a girl) say to her coven member, "That one's a Pink-Sider, no doubt about it."
Huh?
What was a Pink-Sider?
And why did that person think Tiffany was one?
At the end of that first school day, I left the building and was delighted to see Tiffany standing between me and my pedestrian route home. It meant I could get another look at her before dragging myself back to my drab existence as a spoiled-rotten-but-sullen-nonetheless American teenager.
Maybe I would even get to breathe some of the same air Tiffany was breathing.
As I got closer, I began to conjecture about the person or persons Tiffany was waiting for.
Probably some of the cool kids. Maybe she was looking to recruit two or three girls for a mean-girls clique.
Or probably looking for a football player who would take her up to Lookout Point in his Lamborghini and show her his private parts.
Who was she looking for?
Wait.
Was she...?
Could she be...?
Oh!
She was looking at me!!!
{gulp]
Why?
"Hi, Greg," the beautiful doll said sweetly. "My name is Tiffany. I think we live near each other. Could we walk home together?"
Stunned.
Things like that never happened to me.
I gasped out an "OK," then listened all the way home as Tiffany told me how her Dad was a career Army officer who had finally retired in my town. And about all their moves.
My story was weak in comparison.
Lived there all my life. Did well in school. Sports not my thing. Planning to go to college next year and study endophilology.
But she ate it up.
What was happening?
We got to Tiffany's house first and I was afraid she would invite me in. Then disappointed when she said goodbye. Sweetly. And asked if we could walk home again the next day.
I happily agreed.
And we did so for the entire week.
On Friday, as we stopped in front of Tiffany's house, she got serious. "Well, Greg. If you won't say it, I guess I must. Aren't you going to ask me out for tomorrow night? I know you don't have a car, but you could pick me up and we could walk to that little Italian place on Main Street. Then we could come back to my house and...talk. You like to `talk,' don't you, Greg?"
"Talk?" with the most beautiful girl in any high school in America? A date?
I must have looked like a dumbass, but I almost cried when I thanked her and promised to be at her front door at 6:30 the next evening.
I was so happy that Friday at dinner that I forgot to be surly and secretive with my parents. I told them all I knew about Tiffany, which, as it turns out, was very little.
They were a) happy for me and b) stunned that I was involved in meaningful dialogue with them.
The next evening, thank goodness, I didn't embarrass myself on the first part of our date. I dressed in a nice pair of pants and a polo shirt. Boat shoes. Very preppy.
Checking myself out in a mirror before departing for Tiffany's, I was still astounded that she would have taken an interest in me.
I was her height, I imagined, less the heels. Thin. Not much muscle. Cute, but not handsome. Not much body hair. Far from macho.
Wouldn't someone as ultra-femmy as Tiffany want someone super macho?
Apparently not.
I must have been way more charming than I thought.
Oh well. I vowed to enjoy it all while I could.
I met Tiffany's Mom and she was delightful. Then...
Seeing Tiffany descend the staircase was the greatest moment of my life thus far.
She was amazing!
All in pink. Stockings. Stiletto pumps. Minidress.
Amazing.
And she was all mine.
Wasn't she?
She kissed me on the cheek and I almost came in my pants.
Hand-in-hand, for the first time, we walked the three blocks to the restaurant and had a lovely meal together.
I must admit, looking back on it, that I was a bit apprehensive about taking Tiffany home and doing whatever she called "talking."
What were her expectations?
What if [gulp] I were unable to meet them?
That would be a disaster.
As it turned out, I had no cause for that concern. But lots of cause for others.
Tiffany's father was there when we came home. I was expecting a firm handshake from a retired military man and I got it.
He seemed like a nice guy. Though he did seem to check me out physically a bit more than I thought appropriate. And when he said, "Greg's a good choice, Tiffany," I was somewhat disconcerted.
Tiffany "chose" me? For what? And, hey. I was the MAN. I did the CHOOSING.
Not that I said anything like that to him.
I just let Tiffany grab my hand and lead me into the family/TV room.
Where we would be doing that talking, I guessed.
Tiffany sat on the two-seater couch and patted the other seat for me to join her.
I gulped and complied.
Looking back, I suppose she used the remote to turn the TV on, but my penis was getting all the blood my brain should have had.
"I had a really nice time tonight, Greg," Tiffany breathed. "Very nice." And she held my hand.
Time for me to man up, I decided.
Rather than just say I too had a nice time, I leaned forward and kissed Tiffany. On the lips. Closed mouth. Four seconds.
She didn't pull back. I moved forward. And kissed her again. Open mouth. Just a hint of tongue.
My poor cock was outrageous.
And I still wonder why it didn't detonate when she touched it.
She touched it!
Through my pants.
But she touched my cock! And rubbed it as we kissed.
Her knees parted and I slid my hand onto her right inner thigh.
Encased in silky pink stocking.
Warm.
Oh my!
Was that a garter snap? She wore garter belts!!
Our tongues got really ferocious.
And then she stopped.
Oh no!
Was the greatest three minutes of my life at an end?
No.
My life was just beginning.
Tiffany looked at me with what had to be lust and said, "Let's go to my room."
No argument from me on that. I took her hand and she led me upstairs and into paradise.
I was a bit awed at the femininity I saw in Tiffany's room. She oozed femininity, so I shouldn't have been surprised.
Was that a click I heard?
Oh my!
Tiffany had locked the door.
And was asking me to "unzip" her!!
Was she going to take off her clothes?!?!?
In her locked bedroom?!?!?
With me there too!?!?!
I unzipped her pink minidress and watched in delighted awe as she took it over her head, walked to her closet, hung the dress and returned to where I was quivering.
Tiffany gave me the first 1,000-watt smile I had ever seen and it almost blinded me.
Thank goodness I was still able to witness the first sight of her in bra, panties, garters, stockings and heels.
Tiffany amped up the smile by 500 watts and said, "Hey, Mr. Slowpoke. Get undressed. I've been aching for you to make love to me all night and I don't want to wait much longer."
It was a dream.
It had to be a dream.
Stuff like that never happened to me. It never happened to anyone. Except in those long-lost letters to Penthouse magazine.
Dream or not, I got undressed.
To my boxers.
Which were tented by my fatally excited, six-inch ladypleaser. Which was yet to please any ladies. But its luck seemed to have changed.
Tiffany turned away from me for a moment to take off her bra and panties. Getting ready to show me her titties and her pussy with a great flourish, I imagined.
There was a flourish. A big flourish.
Tiffany turned around. Almost shyly. With one arm over her nipples and the other hand over her crotch.
Notice that I said "nipples" and "crotch." Not "titties" and "pussy."
Tiffany's bra was on the floor. Her breast molds were too.
She didn't have breasts.
Tiffany Gusher, the hottest girl of anyone's wettest dream, was a guy!
Oh the horror!
Tiffany sized up my reaction immediately and went into damage-control mode.
"Oh no! Greg, I am so sorry. I thought you knew I was on the Pink Side. Oh, Greg. I'm sorry. I should have figured that in this small town everyone wasn't up on the newest urban trends. I'm sorry. "
And she moved to comfort me.
Taking me into her beautiful arms. Holding me. Rubbing her beautiful nipples against mine. Kissing me.
She didn't feel like a man. As long as she didn't rub that stiffie of hers against me.
Oh.
She had her tongue in my mouth. And she pulled my cock out of my boxers and was rubbing it.
Nicely.
As we kissed.
But she wasn't a girl, she was... a Pink Sider. Whatever that was.
I wasn't gay. I wasn't. But she was so beautiful and feminine.
And she felt so good in my arms.
And she knew just where to rub a cock.
With great hesitation at first, I touched her stiff cock.
And didn't die.
And the earth didn't open and I wasn't flung into hell.
Softly, I caressed her cock and gave her some nice rubs.
It was very nice.
And, judging by her grunts and gasps as we kissed, Tiffany liked it too.
Oh dear.
I wasn't much of a wanker. Once or twice a month. So I had never experienced the kind of big, nasty spermstorm that seemed to be building inside me. I wanted to cum, but I didn't want to look "trigger happy" to Tiffany. I gritted my teeth and thought of dead baby ducks.
"Let's not cum this way, Sweetie. I want to taste you," she half-moaned as she fell to her pretty, pink-stockinged knees.
Oh!
I was being fellated by the most feminine boy on earth.
It was all so "not gay" that I relaxed and just thought of her cock as something that some girls had and some girls didn't.
Whatever lets you sleep nights, right?
Anyway, although I was reaching inside myself for my macho side to take over the proceedings, Tiffany was still in charge.
Who cared what it said on Tiffany's birth certificate?
She was a girl!
Who really knew how to suck a cock.
And was sucking mine most deliciously.
I tried not to make the wrong noises. Wanted to limit the during-fellatio conversation to manly grunts and moans. But somehow, I couldn't stop myself from making little squeals and squeaks. Not to mention squirts.
Which occurred a mere seven minutes into Tiffany's tongue assault on the arrow-point on the underside of my knob.
I had given myself a few minor, black-and-white, whitebread orgasms. But that was an ORGASM!!!
In technicolor.
And three dimensions.
And Tiffany SWALLOWED it all!!!
Oh dear, I thought, as I slid back to the home planet. What do I do now?
Could I suck her cock-like object? Whatever one called it on someone like Tiffany.
Was it time for me to take CHARGE?
Apparently not yet.
Tiffany was licking her lips and saying, "That was delicious, Greg. Let's get into bed and kiss some more and get better acquainted."
Excellent idea. Though I wish it had been mine.
I was naked and Tiffany was wearing only her garters and stockings.
We kissed and sucked each other's tonsils as I ran my fingers all over Tiffany's exquisite body. Including her [gasp] deliciously pink penis and saucy little bag of girlish pearls. I also explored her magnificent ass, even venturing between the cheeks and lightly teasing her tiny anus.
Best Saturday night ever!
It occurred to me at that moment, that I had failed as a gentleman.
Tiffany had given me an orgasm from the Orgasmic Hall of Fame, and she hadn't even cum yet.
Could I take her penis into her mouth, lick her knob and swallow my big reward?
A notion that an hour earlier I would have rejected immediately now seemed like my most immediate need.
So I disengaged from our kiss, slid down Tiffany's body and took her perfect penis into my mouth.
It tasted very nice. And I was delighted to hear Tiffany's appreciative grunts and squeaks as I licked what I knew to be a peener's most sensitive areas.
"Oh, Greggie! That's incredible. Right there! Yes!" my pink angel squealed.
I wasn't fond of the "Greggie" stuff, but I loved that I was exciting my exciting love partner.
And then Tiffany's balls ignited!
And my mouth bulged with her glorious emission.
That made it official.
I was a cocksucker.
And a cocksucker deluxe when I swallowed Tiffany's scrumptious load.
Things were off to a great start.
But a quick ending.
When Tiffany reentered earth's atmosphere, she kissed me hotly.
It was exquisite.
And it convinced me that I would soon be plowing Tiffany's "South 40." Though, considering it now, it would have been a terribly inept effort.
Then Tiffany amended the agenda.
"Oh, Greg, Sweetie. That was amazing! But it's time for you to go home."
I looked at the clock on Tiffany's nightstand. It was 9:30.
Huh?
Tiffany explained.
"That was more than enough for the first date, don't you think? I don't want you to think that I'm one of those easy Pink-Siders who let their men fuck their bottoms five minutes after meeting them. If you want to fuck me, you'll just have to take me out to another nice restaurant, bring me back here, take my panties off, eat me out until I'm soaked and screaming, then plunge your hot, hard cock into my tiny bum until I faint with lust. Sound good?"
Without thinking, I blurted out, "Can we go out again tomorrow night?"
Tiffany giggled. "Sunday is a school night, silly. If we go out on Friday or Saturday, and you're a very good boy, you can sleep over with me."
Then, just from thinking about that fantastic scenario, my cock erupted.
Tiffany gasped. Then laughed with undisguised glee. I joined her. And we set a date for Friday.
Chapter Two – Tested
No homework was ever done as thoroughly as I did my homework over those next six days.
I read just about everything the Internet said about anal sex. Though I was cautious about some of the fiction I read on the subject.
Lubricate, dilate, penetrate, fornicate, ejaculate became my scholastic mantra. I bought the latest issue of Panty Boy magazine, of course, to see how those amazing cream puffs liked it up the old keister. I bought a half gallon of Spermbutt Anal Lubricant, just in case Tiffany and I really hit it off on Friday night.
And I war-gamed how I would take Tiffany to anal ecstasy over and over well into Saturday morning.
That was the objective, wasn't it?
Make my woman crave my cock in her bumhole!
Drive her mad with Greg lust.
Once I figured out how my prick would fit into a place whose like I had never experienced.
Tiffany and I continued to walk home every day. Hand-in-hand that week. I liked that.
We talked about everything but sex.
Though I ached to tell her how gloriously I wanted to fuck her on Friday.
I was so busy learning about anal sex that I neglected to look up that Pink-Sider stuff on the Internet.
I guessed it was some idea about boys acting like girls. Which turned out to be a narrow, but mostly accurate definition.
When Friday finally arrived, I was doubly excited when Dad loaned me the car for my second date with Tiffany,
Maybe she would suck my cock as I was driving. Or in the restaurant parking lot.
Sadly, Tiffany stuck to the same schedule as the previous date.
Happily, she looked even more beautiful, and femininely sexy than the first date.
She wore a light-blue mini-sundress, with brown stockings and light-blue, strappy sandals with a four-inch, pencil heel.
Was I really going to be able to lift those skirts, pull down her panties and SHOVE my manly cock into her furnace of a bum?
I was very hopeful.
That time, Tiffany kissed me as she landed on the bottom of the staircase. Right in front of her Mom and Dad! It was closed mouth, but affectionate.
Oh yeah, I thought. I'm fucking you tonight, Baby!
We left, hand-in-hand. I held the door for Tiffany as she slid her magnificent bottom into Dad's 2008 Ford Fusion. I got a nice look at her stocking tops as she pulled her legs in.
She was so beautiful! I didn't care about that penis-like thing she owned by mistake.
We had a lovely meal and were back at her house at 8:35.
And in her bedroom by 8:45.
Gulp.
Time to put that book-learnin' to work.
Oh no.
I forgot to bring my industrial-strength bottle of Spermbutt Anal Lubricant from the car.
"I saw you had Spermbutt Anal Lubricant in the car, Greggie," my angel said. "No worries. I have some right here."
Whew.
Good thinking, Tiffany.
Wait.
Was it possible that I wasn't Tiffany's "first?"
Hmm.
In the big picture, that was no problem, I guessed.
Though it did put a bit more pressure on me to give a four-star performance.
When Tiffany stripped to her panties and I to my boxers, I earned my first star with some darned good French kissing.
Oooh-la-la!
I was already quite hot and certainly bothered when Tiffany slid my boxers down and entered my bum with an inquisitive finger.
That was new!
Over the past week, I had read so much about being the anal aggressor that I was startled to find myself as the territory being invaded.
It was exquisite! A delightful enhancement of our deep, intense saliva exchange.
I responded in kind, dipping my finger into Tiffany's hot "pussy."
She squealed the way a MAN expects his pantyboy to squeal for her MAN.
That was my second star.
I had a plan for the third star. And the fourth.
The third, I believed would be a bit icky at first. But on our first date, Tiffany had specifically requested a good asseating.
And I had skipped dessert to save room for Tiffany's anal feast.
I took charge.
And placed Tiffany on her hands and knees on the bed. Ass facing me.
She was totally docile to my benevolent orders.
I pulled a chair up to the side of the bed so that I could get comfortable. I was going to eat her ass until she was a squealing, shuddering mess.
I started slowly. Pulling down Tiffany's panties inch by inch. Kissing every pore as I exposed it.
Tiffany grunted and groaned with pleasure. And I hoped a measure of fear.
One must be careful around someone about to engage in cannibalism.
She gave the cutest little squeak when I licked the wrinkle.
Which escalated into louder noises of appreciation as I dug in with my tongue. And my nose. And my fingers.
My greatest fear was that Tiffany's Daddy would gather a SWAT team, break down Tiffany's bedroom door and fill me full of bullet holes to protect his daughter.
A fear that deepened when, after 36 minutes of tongue carnage, Tiffany screamed as if I were slicing her throat and shot the seven thickest cords of cum I ever seen.
It was time for the Spermbutt Anal Lubricant. And my fingers.
I did sort of rush that part, since my cock was begging me to fuck Tiffany. And, as it turned out, so was Tiffany.
I repositioned Tiffany onto her back. The way a MAN pins his woman down when he fucks her. According to the Internet. So true.
I recalled something about the geometry of ass-fucking, so I slid two fat pillows under Tiffany's hips, lined up my angle and pushed my entire cock into her.
Oops.
Was I supposed to do that?
Was inch-by-inch better.
Oh well. Too late.
My technique got Tiffany's attention. She bolted into a semi-sitting position, without losing my cock in her bumhole. And screamed.
Oh dear.
Had I just messed up the best thing in my life ever?
No.
Tiffany threw her arms around me, stuck her tongue down my throat, pulled me back down with her and, by the actions of her hips, not her occupied mouth, begged me to fuck her. Hard.
Yes, ma'am.
We jumped right in to active measures.
To this day, I can't understand how I was able to keep from cumming for 22 delicious minutes and 32 spectacular seconds.
But I did.
And that sealed my fourth star. As well as a permanent plaque in Tiffany's Hall of Fucks.
My angel shuddered through two debilitating orgasms during that 22:32.
And her gratitude was boundless.
She sucked my poopy prick to a second, glorious stand, then "suffered" through an extended, doggy-style fucking that threatened her life force.
That night remains my proudest sex moments as a man.
Notice I didn't say my proudest ever.
Chapter Three – Readied
One week later.
Despite my best efforts to entice Tiffany into seven-days-a-week sex, she followed her "Let's take it slowly" policy. Though it seemed that we were already way beyond what anyone would call slow.
Once one has eaten one's date's ass out and fucked it four times in twelve glorious hours, the ice should be completely defrosted.
Did Tiffany expect that we would be moving on to greater things? If so, I was fully willing.
And Tiffany knew it.
The following Friday evening, Tiffany and I had our typical date – dinner, followed by a trip to her bedroom.
Which was the perfect date. Except for the time wasted on dinner.
Though our dinner conversation proved interesting on that third date.
"You never asked me about how I became a Pink-Sider, Greg," Tiffany stated as our entrees arrived.
A stab of fear pierced my heart.
Had I violated some girlish protocol? Acting insensitive and uninterested? Thus no longer sexworthy???
Think fast, Greg.
I managed to say, with quivering voice, "I was giving you space, Honey. I want to know it all. But I wanted you to be ready to tell me."
Not bad, eh?
I watched Tiffany carefully to see if she bought it. If she didn't...oh, the horror!
One second. Two.
Then a big smile. Followed by a deep kiss. And, "That's so sweet, Greg. You're so sensitive and caring."
Phew!
"Are you ready to tell me now, Sweetheart?" I asked.
Thinking that I would much rather be fucking than talking.
Maybe she would get it all that "feelings stuff" out of her system while we were eating and we would be in the sack within the hour.
No such luck.
But it had to be done.
"I was ten when I realized that I was a girl in a boy's body," Tiffany began.
[Sound familiar?]
Then she went on to describe how she had kept it from her parents until she was twelve. Surprisingly, her super-macho, soldier father was way more caring and sympathetic than her Mom – though Mom came around eventually.
Soon after her "big reveal," Daddy was transferred and it was the perfect opportunity for Tiffany to begin living full-time as a girl.
Daddy did his research, discovered a delightful organization called "The Pink Side," and was able to get Tiffany's documents changed. Thus the former Timothy was then Tiffany – for good.
I wasn't really listening at that point when Tiffany told me about The Pink Side. My balls were aching too much as I thought about getting Tiffany into the sack. But apparently The Pink Side was something like an international "refugee" organization for males who wanted to become all the female they could be. Tiffany seemed to be deeply grateful to them. I remember thinking how spectacular it would be if Tiffany were that grateful to me.
Tiffany pressed on with her story.
Right from the start, Tiffany wasn't like the other girls.
She had EARNED her femininity and was not about to let it dissipate.
Tiffany always dressed as femmy as humanly possible. Always skirts – never pants. Stockings and heels. Lots of well applied make-up. Manis and pedis. Big hair.
Every sensible guy's wettest dream.
Although Tiffany didn't tell me anything about her sexual life from the ages of 12 to 18, she had to be getting all the cock she could ever take in. I didn't want the details. Just wanted to hang onto Tiffany as long as I could.
Because I knew in the sensible side of my brain that Tiffany's infatuation with me had to be temporary.
She was a ten plus girl. And I was, on a good day, a six guy.
So enjoy it while you can, right?
Anyway, there we were. I showed appropriate attention and empathy for Tiffany's story. Which probably extended my potential affair length with Tiffany for two of three weeks.
And it made sweet Tiffany very sexed-up when we FINALLY got back to her bedroom.
What a glorious night it was!
A night to remember.
And not just for the sex.
It proved to be a turning-point night for me. In a way I could have hardly imagined.
Chapter Four – Converted
Eleven p.m., that night.
Tiffany lay next to me.
Naked except for her black stockings and garters.
Chest heaving.
Bum drooling two loads of my sperm.
I lay next to Tiffany.
Naked.
Cock drooling the dregs of two of the best orgasms of anyone's life.
Wondering whether it had all been a dream.
I was never that lucky.
And then things changed.
For the better?
The jury was out at that point.
Tiffany snuggled up to me and asked the life-altering question.
"Greg, Sweetie. Did you ever think about exploring your Pink Side?"
Huh?
What did she say?
I processed. Realized that I may be on dangerous ground. And said, "I don't really have a pink side, Honey."
Tiffany frowned.
Oh no!!
I didn't want Tiffany frowning.
Frowning does not equal sex!
Tiffany relaxed her face and, as if explaining a concept to a small child, said, "Of course you do, Silly. Every man has a pink side. Women have two X chromosomes. Men have an X and a Y. So men are all part Fred and part Ginger – Gingerfred men."
Huh?
What kind of drivel was that?
I should tell Tiffany that she's spouting horse pookie. And then enter a monastery.
Narrowly avoiding celibacy, I said, "Oh. I didn't know that."
Good answer. Though I didn't like where it was going.
Then I found out.
"I'm right and I can PROVE it!" my angel said with a funny little pouty face.
The ground was feeling even more unstable.
But I was unable to argue with someone giving me universe-class pussy.
"How?" I asked, innocently.
"Let me show you," my Sweetie replied.
At which point, Tiffany left our bed of premarital bliss and went to her dresser. She opened a large drawer, rummaged a bit and extracted three items: two stay-up, black stockings and a ridiculously sheer, black, shorty nightie.
As Indiana Jones said at least once in each of his movies, "I've got a bad feeling about this."
Tiffany stood at the side of her bed, thrust her right arm forward and said, "Here. Try these on and tell me what you think."
Oh no.
I couldn't.
She wasn't serious.
Was she?
She seemed serious. Really serious.
Oh no.
There was a serious "no more pussy, Mister" vibe in the air.
One that needed to be snuffed out quickly.
Very quickly.
By surrender. Or fierce, manly refusal.
I chose wisely.
I accepted my short-term fate and preserved my long-term pussy prospects.
Grumbling just enough to show that because of my boundless virility, I was just going along to get along.
Tiffany was delighted.
Females, with or without cocks, love imposing their will on men.
She graciously showed me how to roll up each stocking and ease it up my leg.
Oh no.
That was bad.
It felt good. Even on my hairy leg.
Cool and comfy.
And, as a person with a lifelong stocking fetish, it felt like a bucket list item being checked off.
Oh no.
I was starting to erect!
So I hustled to get the nightie on to cover my growing humiliation.
Bad move.
The nightie wasn't nearly long enough to cover my stiffie.
And wearing the nightie made the situation much WORSE!
It felt delightful.
And, as the full-length mirror that Tiffany dragged me to prove, it looked even better.
I didn't want to be obvious about the pleasure I felt from my first "dressing" experience. But I just had to stare and sigh. And preen and sigh. And look at my rear reflection and sigh.
But I could have concocted a story to explain that away.
When I shot my spunk, just from looking at myself, Tiffany had clearly made her point.
I apparently did have a "pink side."
Now what?
Tiffany knew what.
"Oh, Greggie, you're so cute and kissable like that. Let's lie down, kiss and cuddle and see what happens."
Since "what happens" had always been spunktacular with Tiffany, I cooperated.
Though warily.
Something new was definitely afoot.
I thought about asking Tiffany if I could remove my girlie stuff and just fuck. But I sensed that if I didn't follow Tiffany's agenda, fucks weren't happening.
Plus, being in that girlie gear was surprisingly exciting to me.
So I lay down and watched with curiosity as Tiffany slathered a big dollop of Spermbutt Anal Lubricant onto the middle and ring fingers of her right hand.
My optimistic assumption was that Tiffany would be getting her pussy all nice and slick for me. Saving me the effort.
I was wrong.
Really wrong.
Tiffany got into bed and asked me to lie on my back and open my legs.
I almost asked why. But I complied.
Tiffany rewarded my obedience with a totally delicious kiss that lasted for five minutes.
The first minute of which was a delight.
The last four minutes of which were life-altering.
Tiffany slid two fingers into my virginal anus.
Nothing had ever invaded that space from the outside.
My prostate had never been touched.
Even by a doctor.
Dr. Tiffany changed all that.
She knew exactly where my prostate was. She knew exactly what to do with it once she found it.
I yelped.
Then I wiggled, half trying to get away. Without breaking the kiss.
The other half of me was delighted with the sensation. Then all of me was.
Oh dear.
My first anal sex was only with Tiffany's fingers. But it was amazingly spectacular.
I was grunting and gasping as Tiffany broke our kiss and looked at my teary eyes. She was smiling her wonderful smile and saying something I couldn't comprehend because all my senses except my seventh sense [my asshole] had shut down.
Tiffany never actually touched my penis during my erotic agony.
But I was still flung off Cum Cliff.
And it was a long way down.
My anal orgasm lasted an amazingly long time. And my cum drooled more than it leaped.
But it was splendid.
Which is not a superlative, because I was far from sure about how I felt about what just happened.
It seemed pretty obvious to me that I had lost some of my macho cachet with Tiffany. Assuming that I ever had any. Because she seemed to have lured me in with DNA-scrambling sex, then edged me toward what she called The Pink Side.
Acting like a girl. Or how a girl is supposed to act.
Wearing sexy clothes. Being admired. Desired. Lusted after. Having lots of sexy sex.
Though the sex we were having had an element, perhaps just a whiff, of gayness about it. Since Tiffany and I each had one of those penis things.
But perhaps I was being overly critical.
Tiffany and I were having fun. The way 18-year-old are supposed to have fun. Experimenting. Dipping our toes into things. And our penises too.
OK. Rationalization successful, I faced Tiffany's interrogation.
"Did you like that, Greg?"
I tried to speak but could only nod in the affirmative.
I looked at Tiffany and saw no guile. Only love for me.
But, truth be told, I wasn't really able to focus my eyes at that point.
I braced myself for further questioning.
Tiffany gave me a nuclear smile and said, "Good. Let's take a little nap. When we wake up, you can fuck me. Then we'll nap again and you can fuck me again. Sound good to you?"
I nodded again. Astonished and exhausted, I nodded off.
Tiffany was good to her word.
I spent the next day at home telling my parents a censored account of my sleepover at Tiffany's.
They were cool with me having sex, now that I was 18. But Mom cautioned me about getting Tiffany preggers.
I assured Mom as tactfully as I could that that was highly unlikely.
I reported for our Saturday night date in a state of sexual heat and sexual fear. A delicious combination under most circumstances. But I wasn't sure of Tiffany's intentions at that point.
We skipped dinner and went straight to Tiffany's room.
My angel stripped to her black stockings, garters, and heels and put on the cutest matching babydoll with tiny pink ribbon accents.
My prick was bursting in my boxers and as I shucked my last garment, I was delighted to see Tiffany on her knees, giving me her usual life-threatening blowjob.
You see, I was afraid that she was going to try and get me to do that girlie dress-up thing again. Which I didn't want. No sir.
Didn't want anybody rubbing my prostate. No way.
Oh. She was extra sexy with her BJ that evening. And I didn't object when she brought me to conclusion by inserting her middle finger in my anus. Just one finger. No prostate massage. Because I didn't want that.
I should have seen what was coming next.
Tiffany had me in the post-orgasm-but-wanting-lots-more-orgasms stage. Which is usually docile.
"Let's go into my en suite bathroom and I'll shave your legs, Greg," she said. "You'll be amazed at how good the stockings feel with shaved legs."
Time to stand up and be a man.
A celibate man. But a man.
Of course, I had to admit that the stockings and nightie thing had felt good the night before. And that led to lots of sex with Tiffany.
I followed.
And submitted to it all.
The leg-shaving.
Even to Tiffany dressing me in pink, seamed, fully-fashioned, reinforced-heel-and-toe stockings; which had to be held up with a pink garter belt. As she slid the pink babydoll over my head, I felt diminished as a man. But extraordinarily randy as a sissyboy.
Pink.
I was wearing pink lingerie.
And it felt incredible.
I looked incredible. More so after I [blush] allowed Tiffany to use lipstick and a little blush on my face,
I was almost pretty.
OK. I was pretty.
And my cock was outrageous.
I stood at Tiffany's full-length mirror and drank in the faux-femme me.
Perhaps for too long a time period.
If I were thinking about expressing my outrage to Tiffany.
Tiffany came up behind me and kissed my neck as she slid her Spermbutt Anal Lubricant-slicked fingers into my bumhole.
Oh dear.
Was Tiffany going to massage me to another debilitating, anal orgasm?
She wasn't using the same angle as the previous evening. No real prostate persecution.
But it still felt good.
Tiffany asked me to join her on the bed,
"Get on all fours, Honey," Tiffany said. "I've got something you'll really like."
I was horribly naïve at that point. I thought she was going to do that prostate thing as she stroked my cock to a monster cum.
Not exactly.
I couldn't see what Tiffany was doing at that point. I later found out that she was slathering Spermbutt Anal Lubricant onto her stiff prick.
Stupid me. I even thought that when her cockhead parted the entrance to my anus, Tiffany was using three or four fingers.
When she shoved the entirety of her five-inch sissy pole into me, I screamed like a banshee girl at a horror movie.
Good thing that Tiffany's parents were out.
Tiffany was fucking me!
I was being fucked!
Like a girl.
By a girl.
And, darn it, I liked it.
No, I loved it.
Crazily enough, the pressure on my prostate from Tiffany's stiffie, though cataclysmic, wasn't the high point of being fucked for me.
I loved giving myself to my fucker!
Which sounded awfully pink-sider to me.
Oh dear!
What did that mean?
What were the long-term implications?
Murky.
What were the short-term implications?
Crystal clear.
I was cumming my femmed-up guts out.
Bazinga!
I was so obliterated by orgasm that I hardly noticed when Tiffany filled my bum with cum.
My life would never be the same,
Tiffany seemed both happy for me and proud of herself as we kissed and cuddled post-coitally.
At that point, I was still unclear why she would feel either emotion.
I tried to hide my tears from Tiffany, but she noticed.
Oh no!
I was such a little nancyboy.
Not the world-class, stud lover I wanted to be for Tiffany.
But my tears of confusion and loss and love and uncertainty tugged at Tiffany's heart.
And, I believe, it was when she began to truly love me.
Not in the traditional, man-woman way. In a different way. But love nevertheless.
We cuddled and kissed wordlessly for a long time. Long enough for me to get an outrageous stiffie.
Tiffany wiggled her bum at me and I accepted her invitation eagerly. I was in to the hairs. Plowing Tiffany's bottom like a man plows his woman. Except for what I was wearing and the sissy squeals I was making as I approached my bonecrusher orgasm.
That was more like it!
Back on top!
Until 35 minutes later when I was on my back, legs back and up, grunting girlishly as Tiffany satisfied a deep hunger in my greedy bum.
Confusion!
Conflicting viewpoints.
Shame.
Guilt.
But some magnificent orgasms in both roles.
We kind of traded fucks like that off and on all night until 7 a.m. Sunday morning. At which time, Tiffany asked that I shower up and leave.
I did so. Staggering home with only a promise to walk Tiffany to and from school all week.
That week, I tried to get Tiffany talking about what had happened and what was coming up.
But all I got was, on Thursday, she agreed to have me over for our Friday night date, right after school.
That was great! Three extra hours of sex time with Tiffany. Even if I did have to do some girlie things.
Things that I adored. But was ashamed of.
Walking home with Tiffany that Friday, with my anticipatory erection almost ripping my pants, Tiffany got personal at last.
"I haven't told anyone this, but Daddy isn't my biological father," my Love Angel shared. "My bio father left us when I was three and Daddy married my Mom when I was five. I love him and consider him my real Daddy."
Interesting, I thought. But irrelevant when all I could think of was imminent sex.
Or so I thought.
We walked into Tiffany's house at 3:05 that Friday afternoon. No one else was there.
I wanted to get Tiffany to her room by 3:06 and my cock in her mouth or bum no later than 3:11.
Not Tiffany's plan.
We arrived in Tiffany's room by 3:06, but didn't get it on right away.
"Let's go all the way with our pink sides before we go all the way," she said.
I grumbled softly. Just enough to suggest that I didn't want to do lingerie and make-up.
I WANTED that. ALL of that. Followed by some girlie on girlie sex.
Just as I has been fantasizing about every night of that week. As I was giving myself a nice, good-night wank.
Tiffany giggled at my grumbling and said, "I think you'll like tonight's fun. All of it, Sweetie."
I shuddered with lust.
And kept shuddering as Tiffany supervised my leg and armpit shaving. Then a solo shower. With no consideration to my aching erection.
My lover took great delight in dressing me that Friday.
I almost spunked, of course when she had me slide on a pair of white, seamed, fully-fashioned, reinforced-heel-and-toe stockings. Then when I hooked them onto my white, super-femmy garter belt.
I wore my first bra that night. White, of course. Without breast forms. Which made the silky material rub my nipples.
Oh!
Tiffany tried and mostly succeeded in having me walk in 2.5-inch white, spike sandals.
It was 4:01 and no relief yet for my throbbing throbber.
But I liked what I saw and what I felt so far.
Then Tiffany set to work on my make-up. Way beyond the lipstick and blush of the previous weekend.
She did some magic with foundation on my face. Then she abbracaddabraed my eyes! They were so big and beautiful!
Then she slid a white, shortie nightie on me and, surprise – a seriously beautiful, seriously blonde wig.
Oh my!!
I was so captivated by my amazing, girlish beauty in the mirror that I hardly noticed Tiffany slipping a white peignoir on me.
I also didn't notice when Tiffany, who was dressed only in her short, pink nightie, had left the room.
But I did notice, three or four minutes later, when I heard a deep, masculine voice saying, "You look amazingly beautiful, Greg."
Oh no!!!
Horror!!!
It was Mr. Gusher!!!
Tiffany's Daddy!
Who was a man.
Looking at the femmy me!
My life was over.
Shame.
Guilt.
I was bound for Crossdressers' Prison for sure. After I was paraded through the streets for public mockery.
But wait.
Did he say I was beautiful?
Oh my.
I was, wasn't I?
But he was a man!
And he would...
Wait.
What would he do?
Probably nothing like exposing me. Tiffany was a crossdresser and he didn't expose her.
Oh no!
What if he wanted to "do things" with me?
The things a man does with someone as beautiful and feminine as I was.
The horror!
Mostly.
Why was my cock stiff thinking about "doing things" with Mr. Gusher?
Tiffany broke my panicked chain of thought.
"I've been telling Daddy how beautiful you're becoming, Greg, and I just had to show him. Don't worry. He's not going to say anything about you, even to my Mom. She's visiting her sister this weekend anyway."
"It's true, Greg," Mr. Gusher said. "Tiffany described you as so beautiful that I just had to see for myself."
OK. Makes sense, I thought. If you got a beautiful new car or something, you would want to show it off.
I was that beautiful.
I liked that. But I wished Mr. Gusher would leave. Tiffany and I had some serious fucking to do. And I was NOT going to fuck Mr. Gusher's stepdaughter in front of him. Nor would I be fucked by Tiffany with him in the audience, neither. Good thing I remembered that.
But Tiffany and her Daddy had their own agenda for that Friday night.
"Greg, I don't want to call you that anymore when you're dressed so femmy," Tiffany said. "May I call you Jennifer?"
Jennifer?
OK
Jennifer.
I nodded weakly. Looking cautiously at Mr. Gusher. Seeing if he was making any moves to leave.
Not yet.
Tiffany cheered, clapped and gave me a big kiss.
Then she dropped another bomb.
"Jennifer, now that I know that you lean toward your pink side...no, Jennifer...don't protest. You know it's true. Now that I know. I want to show you how to keep healthy. Daddy."
Mr. Gusher spoke. "Jennifer, a pantyboy like you or Tiffany, needs to be `emptied' before she goes to sleep each night. Or she could injure herself. Now I know you probably do a self-emptying each night before sleeping, am I right, Jennifer?"
I blushed.
"I thought so. Anyway, self-emptying is rarely complete. And It's far from ideal from a medical perspective. Trust me on this. It's on the Internet. A pantyboy's best emptying comes from a man. A real man. It's OK, even preferred, if it's her Daddy. But there are incest limits, as you'll see. Tiffany and I have no incest limits, but we impose some limits anyway. Too much talk. Let me show you. Let's pretend it's bedtime for Tiffany and I'm ready to tuck her in. I come into her room, sit in her comfy chair and she sits her deliciously bare bum on my lap..."
Which was what they did.
My cock stirred as I watched stepfather and daughter French kiss as voraciously as the storming of the Bastille.
They broke the kiss and Tiffany exposed her fiercely angry penis to Daddy's loving hand.
Mr. Gusher stroked it beautifully as he consumed Tiffany with kisses.
Tiffany grunted and squeaked as Mr. Gusher's talented fingers brought her to the edge and then, with a desperate squeal, Tiffany deluged her stepdaddy's hairy paw with her sweet cream.
Tiffany's pleasure was obviously immense, since she obviously loved her Daddy.
They kissed hungrily, but the fun wasn't over.
Mr. Gusher had Tiffany stand in front of him as he licked her sperm from his fingers. Then he set to work licking up what had shot to her belly.
Of course, there was still sperm dripping from her penis, so after giving her balls a fine licking, Daddy consumed Tiffany's droopy cock with his mouth.
Tiffany was barely able to balance on her four-inch stilettos as Daddy gave her a blowjob to remember. Ending in a screaming, heaving orgasm down Daddy's throat.
They kissed for a while after that until Mr. Gusher said to me, "That was a 50- 75% emptying, Jennifer. I wanted Tiffany to save some for you before the two of you took your first recharging nap. Did you enjoy that, Tiffany?"
"Oh, yes, Daddy. You're amazing! Will you show Jennifer how a proper, bedtime emptying is done?"
What?
Me?
Mr. Gusher wanted to "empty" me?
Wasn't that wrong?
Wouldn't that be gay?
Why was I sitting on his lap, letting him kiss me? As he stroked my penis?
Why did I locate his manly penis and stroke it as he kissed and masturbated me? An act that drew more applause from spectator Tiffany.
Oh my!
Mr. Gusher was an excellent kisser. And an awfully good cock-stroker.
But what was I letting happen to me?
I had stepped over a line when I started in with Tiffany. That was boy-mostly girl sex. We moved to semi-girl-mostly girl sex. Then to mostly girl-mostly girl sex.
And there I was.
Mostly girl-man sex.
And I was the mostly girl.
Submitting to Mr. Gusher's exciting fondling and tonguey kissing.
And loving it.
I felt desirable.
I felt needed.
I felt sexy.
And I felt my balls telling me that they had never been so excited.
Then my balls expressed themselves the way they communicate best.
I screamed like a pathetic little sissyboy as I blasted my sperm all over Mr. Gusher's hand and arm and my tummy and white babydoll.
I stopped wanking Mr. Gusher as I evacuated my testicles.
Why was I disappointed that I hadn't made him cum?
I shouldn't even have been touching him "down there."
I was a young man, wasn't I? I mean it's OK to dress up a little for a date, isn't it? Doesn't change your status from "fiercely hetero" to "voraciously sissy/gay/pantyboy faggot," does it?
So why, despite all that deep thinking and creative rationalization, did I sink to my knees and take Mr. Gusher's fat cock into my mouth?
I guess because I wanted to.
It pleased Tiffany greatly that my tongue was torturing the arrow point under Mr. Gusher's knob. But I wasn't sucking him off to please Tiffany. I was sucking him off to please me.
His masculine taste and smell were intense.
His cock was the food I had craved all my life but had never had.
And he seemed to know it.
His cock was terribly excited. And so was the rest of him.
It was so big and hot and hard.
My guess was that Tiffany didn't limit herself to being the receiver of her stepdaddy's sexual favors.
Mr. Gusher didn't impress me as a chump who gives and never receives.
Regardless, he was going to receive from me. and I was about to receive from him.
Mr. Gusher cried out so loudly that even Tiffany (as she told me later) was startled.
And he unleashed the sperms of war.
Down my delighted throat.
Yum.
I had made a man cum.
No.
I had made a man cum within a micron of his life.
I was THAT beautiful.
And THAT sexy.
My only two tiny regrets were 1) that Tiffany would be jealous of the way I could satisfy her Daddy and 2) that I would probably have to scratch out the eyes of both Tiffany and her mother if they tried to get between me and my new man.
Upon a bit of further reflection, it occurred to me that there were other men, billions of them, who would be aroused by Jennifer.
Jennifer was me, remember.
So maybe I would allow Tiffany and Mrs. Gusher some access to Mr. Gusher.
Anyway, the way I figured it, I would just suck Mr. Gusher to a second stand, get onto my back, lift and spread my legs and let Mr. Gusher go to town on me.
So imagine my disappointment when he got up, tucked his cock away, kissed me on the lips, did the same for Tiffany and said, "That was awesome, Jennifer. You too, Tiffany. Have a good night, girls. See you tomorrow."
Huh?
He was leaving?
I looked at Tiffany. She was looking at me with a pouty face.
Oh no. I was once again in a delicate situation.
"Why are you so disappointed that Daddy's leaving, Jennifer? Don't you want to make love to me all night?"
Carefully, Jennifer.
I cleared my throat, considered my future and said, "Of course I want you, Baby. All of you. I just felt bad that your Daddy didn't want to fuck me. Am I ugly?"
Tiffany giggled.
Whew.
"You're insanely beautiful. Almost as gorgeous as me. Daddy was being a gentleman. A gentleman doesn't put his prick up his girl's bum until the second date."
I considered that.
Then I asked, "Will tomorrow be our second date?"
Tiffany laughed hard.
"Of course, Sweetie. Mom won't be back until Sunday. Since you're all steamed up, may I fuck you. Watching you and Daddy got me all horned up."
It was true.
Tiffany's cock was titanium hard.
I kissed her and got on all fours.
She was in to the hairs five seconds later.
Yum.
Chapter Five – Pink Sided
What a Friday night!
I wanted to stay the weekend with Tiffany and Mr. Gusher, (on that second date) but Tiffany scooted me home at noon on Saturday.
Which was probably wise for my health.
Though my plan to take a four-hour nap at home was thwarted when I saw an SUV in our driveway.
Who was that?
I went into the house, hoping to slip upstairs and under the covers.
But Mom intercepted me.
"Oh, Greg. There you are. Good. Or should I call you `Jennifer?' Don't worry. Your father and I will catch on to all this. Come see our lovely visitor. Heather from The Pink Side."
OK.
No one on earth should ever be as surprised as I was with all that was in that paragraph from Mom.
Mom and Dad KNEW I was a cocksucking crossdresser named "Jennifer?"
They accepted it all?
Someone was at the house from The Pink Side? Recruiting me or something?
My head was about to explode.
I barely remember following Mom into our living room where Dad was sitting with a stunner of a babe Mom had said was named Heather.
Oh my!
Dad was sitting, but I'm almost sure that he had a Heather-induced hardon.
Moments later, so did I.
Heather was just short of six-feet tall. In her four-inch heels, she was a good six-three.
Her legs, enclosed in amazingly sheer, black stockings, were spectacular.
As was her ass.
And her perfectly made-up face.
Not to mention her DD-cup titties. Or her bimbo-length blonde hair.
But Heather was no bimbo.
She greeted me with a gleaming smile and said, "Wonderful to meet you, Jennifer. Tiffany and her Daddy have been telling me great things about you. Seeing you in person, I can see that they didn't exaggerate."
I blushed.
Then I remembered that I was in Greg clothes. How did Heather know I was a babe as Jennifer?
"I know what you're thinking, Jennifer," Heather said accurately. "You're wondering how I know what a knockout you are en femme. Two reasons. First, meeting with pre-trained Pink Siders is my job. I can almost smell femininity. Second, Tiffany sent me lots of pics and videos she took of you with hidden cameras. You're an amazing lover, Jennifer. I hope we can get together some time."
OMG!
She said that in front of my parents.
Of course she had also told them that I dressed as a girl named Jennifer and had intense, full-body sex with a shemale named Tiffany. Had she told them about Tiffany's Daddy?
"Full disclosure, Jennifer," Heather said, "I also told them about your fun with Mr. Gusher and how you hope that he'll fuck you later today."
It was inevitable.
I cried.
What was the song? "I felt all flushed with fever. Embarrassed by the crowd. I felt she took my letters and read each one out loud."
I knew the feeling.
Mom held me in her arms to comfort me.
"It's OK, Honey. Once you've had your Pink Side training and you're all girl all the time, there will be LOTS of men who will want to love you. And fuck you of course. Heather showed us the pictures. You're an amazing beauty. Daddy and I are so proud. Daddy has even volunteered to `empty' you on school nights so you can sleep well. Won't that be nice for both of you?"
Slammed down by the burdens of my new, shocking circumstances, I collapsed into a chair.
Was I still on my home planet?
Had the culture really accepted transgenderism that much?
And who were the space aliens who had occupied my parents' bodies?
"Pink Siders live awesome, fun-filled, financially-secure lives, Jennifer," Daddy said.
Oh.
Was I calling him "Daddy" now? And was he going along because he thought it was the best thing for my future? Or did he just want to French kiss and wank me five nights a week?
Probably both.
I had to sit.
Heather sat next to me and waited until I had collected some of my wits.
"With your permission, Jennifer, you'll be attending Pink Side classes Monday through Thursday afternoons after school. You'll learn all about cosmetics, fashion, and general femininity subjects such as walking in heels, feminine mannerisms and flirting with men. And don't worry. We take two sex breaks during each training session in order to cool you off so you can concentrate on learning."
I blinked. It sounded awesome.
Mom jumped in with logistics. "It's all paid for by the Pink Side Foundation, Honey. The Foundation was established by a billionaire who loves pantyboys. They even pick you up from school every day in a pink limo. And during the first year of membership, you get an open account at Timmy's Girlish Secret for lingerie, sleepwear, stockings, big heels. Everything except street clothes like dresses and skirts. Daddy and I will buy those for you."
Street clothes? Why would I want those? Did they think I would be going out in public as Jennifer? I couldn't!!
But Mom wouldn't be denied. "Heather says the training should take about three months, after which you can start going to school as Jennifer. Oh, I can't wait to start shopping for prom dresses with you. I'll bet your handsome classmate, Mark Hardwood, will ask you."
There it was. My future as dictated by Mom, Daddy and that Heather person.
Trouble was, it all sounded wonderful to me.
"Are you OK with all that, Jennifer?" Daddy asked. "Do you need emptying."
Daddy sounded a little too eager for that.
"I'm OK with that, Mom and Daddy. No emptying yet though. Please let me be alone for a bit so I can process all this and take a nap."
Mom said, "Of course, Honey. You need your rest. Mr. Gusher is going to fuck you tonight. Probably all night. And you want to be in tip top shape for that."
It was official. The world had gone meshugana.
But I did need sleep.
Surprisingly, it came to me quickly. When I awoke at 4 p.m., Heather was gone. I hustled to take a shower and shave my legs and armpits, then scooted downstairs to say goodbye to Mom and Daddy.
It was a little disconcerting when Mom said, "Use plenty of Spermbutt Anal Lubricant and make sure Mr. Gusher uses it on his cock too. And his cock will go into you more easily if you move your anal muscles as if you're voiding."
Thinking back, I think I preferred when Mom would ask where I was going and I would sullenly grunt out an "Out."
It was the agreed upon hour of five p.m. when I knocked on Tiffany's door and was greeted by my beautiful angel.
Oh my. She looked extra sexy that night. Her makeup was the most dramatic (slutty) I had seen it. And she was all in black lingerie and heels. As legend goes, when a girl wears black lingerie, she wants to get fucked.
Tiffany whisked me in and gave me a big kiss. Three minutes later, we were in her room. I was naked and she was on her knees sucking my cock.
That's what I'm talking about!
Seven minutes later, Tiffany swallowed my creamy emission, stood up and kissed me.
Then we went to work.
She femmed me up as she congratulated me on my commitment to the Pink Side program.
And she revealed her motivation for taking me on as a project.
"Greg is a very nice young man," Tiffany said, "and I liked him very much. Probably loved him. But Jennifer and I will be soulmates. BFFs at school. Somebody our age to hang out with who isn't one of those unfeminine creatures who happen to have vaginas. Plus, we'll have so much fun meeting boys and men and going out with them."
Going out?
Did Tiffany think she and I would be dating men and boys? Double dates? With sex? Lots of sex?
Oh!
It was all happening so fast. Would I be ready for that in three months?
Would I be ready for that in an hour or so?
Mr. Gusher loomed over my evening.
Once Tiffany pronounced me ready.
Tiffany stepped back and admired her work on me.
"Not bad," she said. "Daddy's cock will be ripping his pants when he sees you. Next Friday, after a week at Pink Side training, you can get yourself femmed up."
I couldn't wait to see how I looked.
Oh!
I was exquisite!
I was all in pink lingerie and stockings. My eyes looked enormous. My legs invited spreading. I was even wearing powderpuff slippers with a four-inch-stiletto heel.
Tiffany considered a wig, but decided on pink barrettes and a ribbon.
I almost spunked at my own reflection. Which I admired for a narcissistically long time.
So long that, once again, I didn't see Mr. Gusher, my fucker-to be, enter the room.
He groaned with lust.
I heard that.
And spun around to see him naked and rampant.
Oh dear.
It was too much.
I shot six thick strands of sissy juice into the air.
Mr. Gusher smiled.
"Now that's the kind of greeting I like," he said.
I blushed with embarrassment.
Tiffany giggled and said, "Have fun, you two. I'll see you tomorrow."
Tiffany was wearing a pretty black dress. She was going out!
Why?
"I have a date, Jennifer. You have one tonight and so do I. I'll be home by 9 a.m., Daddy."
"Have fun, Honey," Mr. Gusher said. "I know we will,"
OK.
That was the moment.
I knew it was the moment.
The moment for me to choose my future.
I could have just said no. Wiped off the makeup. Put my Greg clothes on. Gone home and told Mom and Dad I changed my mind.
If I didn't do that, I had really accepted my Pink Side. For life.
It was no contest.
I stepped forward and let Mr. Gusher consume me with tongue kisses. And warm, delicious hugs.
He wanted me!
I wanted to be wanted.
Oh!
He was so manly!
So nakedly manly!
All of him.
I was just a powerless little sissyboy. Subject to all of Mr. Gusher's filthy lust.
It was the best, girls!!
He started out with some fierce tongue-duels.
I love those.
Then, to show me his manly power, he picked me up and flung me onto Tiffany's bed.
On my back!
Helpless!
Would he mount me right away? And fuck me dry?
I didn't want that.
I mean I wanted it, but it wasn't my first choice.
I was relieved when I discovered his true plan.
He spread my legs and dove his face between my thighs. Sucked my balls for a glorious minute or two. Then went after his real objective.
My pussy.
Oh.
Tiffany had never eaten me out before she fucked me.
Though I had eaten her several times. I would have to speak to her about that.
Right after I stopped screaming from Mr. Gusher's cannibalistic onslaught.
The man could eat ass!!
And I loved having my ass eaten.
His tongue gave me unimagined delights. And my testicles showed their appreciation with a seven-spurt salute.
My ass responded by opening its petals for him.
It occurred to me that perhaps Mr. Gusher had honed his anilingual skills on his stepdaughter, Tiffany.
And didn't Tiffany make ass eating a necessary prelude for our first fuck.
Then I stopped thinking.
I was sloppy wet after 23 minutes of anal consumption.
Mr. Gusher's face was soaked.
No matter, I kissed him with full tongue in full gratitude.
As we kissed, he mounted me. Face to face. Me on my back.
Helpless.
I gasped as I felt his cock at my girlish gate.
I shuddered in terror.
It was too big.
I was going to die, just as I was really starting to enjoy my life.
But no.
Mr. Gusher's cock pinched as it went in. But no real pain.
Just incredible pleasure.
Every fuckstroke scraped my tender prostate.
I felt his hairy chest rub my tender nipples.
And his tongue licked my tonsils.
It was the greatest 31 minutes of my life.
Ending, for my man, with a cum so spectacular that he claimed to walk to a bright light at its conclusion.
I, of course, expressed my appreciation for my lover man's efforts by spunking at the 8th, 17th and 31st minutes of my first man-sissy fuck.
Somehow I survived that night, walking home bowlegged at 9:35 the next morning. Wearing a broad smile. Committed to the Pink Side.
Chapter Six – Full Transition
That Friday night began what I guess you would call my "training routine."
Not that it was a boring routine.
It was a great time in my life. And it went like this.
Sissy on sissy sex with Tiffany every Friday night.
Man on sissy sex with Mr. Gusher every Saturday. (Somehow, Mrs. Gusher always seemed to be at her sister's each weekend.)
Sundays were for rest and shopping with Mom at Timmy's Girlish Secret for lingerie, cosmetics and all sorts of sissygirl stuff.
Monday through Thursday afternoons were for training at a nearby Pink Side location.
But I must mention the importance of bedtimes from Sunday to Thursday.
That was when my Daddy, for purely medicinal purposes, "emptied" me so I could sleep properly.
I particularly remember that first Sunday bedtime. The night after Mr. Gusher and I first fucked.
Since Mr. Gusher hadn't allowed much sleep that fuck-filled night, I took a long nap that Sunday afternoon. Getting up at dinner time.
Mom made a nice pork roast with mashed potatoes and canned corn.
Daddy seemed a bit distracted, even though I dressed as Greg, not Jennifer.
I guess I still looked sexy in a tshirt and Bermuda shorts.
I said good night to everyone at 9 p.m. and asked Daddy if he could help me as he promised at about 9:30.
That night, I only had some the starter lingerie sets that Heather had left, no street clothes yet.
Nevertheless, I got ready for Daddy. I was all in yellow: babydoll with matching panties and stay-up stockings.
Was I being naughty by putting on lipstick? And a little blush?
I think my inner cockteaser was emerging.
At 9:30, there was a soft knock on my bedroom door. I asked Daddy to come in.
He opened the door.
Poor Daddy.
The sight of me was a bit overwhelming.
The poor man was visibly aroused.
And nervous.
But he had a duty to perform and a promise to keep.
Was he carrying a big bottle of Slickyboy Masturbation Cream (a Spermbutt Industries product)?
He was.
Way to go, Daddy!
He was obviously serious about doing a good, thorough job. Though. Truth be told, I was so randy about being en femme with Daddy that I probably would have cum the second he touched my stiffie. If not before!
Daddy set the Slickyboy Masturbation Cream down on my nightstand and said, "Please take your panties off and lie on your back, Honey?"
My cock twitched at that "Honey" name.
He had never called Greg that.
Lesson: want good relations with parents? Get into a babydoll and let them jerk you off.
See? Porn can be educational.
Anyway, Daddy was trembling a little as I turned away from him and very shyly pulled my panties down and off. Giving Daddy a nice view of what Mr. Gusher said was the best pussy he had ever fucked.
I was such a tease. I even made sure, in my "struggle" to de-panty from the standing position, I showed Daddy a little "pink."
I'm pretty sure I heard him gasp.
As I turned to face Daddy, I sort of half-covered my exposed penis with my hand. But I was so stiff and drippy that there was more cock than hand.
I lay on the bed, on my back, on the side that right-handed Daddy would have better access to my "sissy bits."
Another gasp as I withdrew my hand and lifted my nightie above my nipples. To avoid cummage on the nightie. And to heat Daddy up some more.
Daddy took a moment for some reverent staring before he lubed his right hand with lots of Slickyboy Masturbation Cream.
Carefully, lovingly, he began to lubricate my ballsack.
I cried out girlishly, but managed not to cum.
I wasn't too concerned about cumming too soon, thus chasing Daddy off, because the mission was emptying and one cum wouldn't do that.
Daddy had very talented fingers on my little pearls. He caressed each one with wonder and admiration. Then he moved his slick hand up my shaft. Slowly. Until he reached my knob. Which was almost purple with excitement.
Daddy skinned me back all the way and used his thumb on the underside of my knob. In the most sensitive spot.
OH!
It was exquisite!
Of course, many sissies dream of doing naughties with Daddy. I was living that dream.
Three minutes was all I could stand of that delicious agony. So I screamed and spunked wildly. All the way up to my chin.
A peek at Daddy showed me that he was justly proud of himself.
But the emptying was not over.
Improvising nicely, Daddy used his fingertips to gently spread my cum, which had drenched my chest and tummy, all over my erect nipples.
He moved me to erotic overload when he tickled my resurging prick with his other hand as he tortured my nipples.
Bad Daddy!
My eyes were wide open.
I tried to gasp out a "Slow down, Daddy, before you kill me with love!"
But all I could do was scream and cream.
Lots of cream.
And an orgasm so intense that the state had my bedroom declared a disaster area.
But the Beast wasn't done with me yet.
The bad man slid two well-slicked fingers up my bum and agonized my prostate until I drooled out four watery drops of semen.
I was empty! In 22 minutes and 17 seconds.
I wanted to tell Daddy that he should double my life insurance policy. But he was kissing me good night.
No tongue.
I wanted tongue.
And I wanted to suck Daddy's cock in gratitude.
He never did let me suck him off. Though, as then weeks went by, we did evolve into some lovely tongue-kissing and, in the third week, Daddy began to let me masturbate him.
I loved it! He loved it. But that was as far as we ever went.
Don't feel too bad for Daddy.
Four weeks into my training, Tiffany invited Daddy over for some Saturday night fun as Mr. Gusher and I gushed and gushed.
Mom was Ok with that, as long as she could have Sundays with me to use that open account at Timmy's Girlish Secret.
Mom and I bought some beautiful, super-sexy lingerie as well as some lovely outfits I could wear in public even though none of that was covered by The Pink Side. She was especially eying down the prom dresses and the wedding gowns. Even though no one at school knew I was a girl yet. And I sure wasn't getting into a wedding gown soon.
Pink Side training was a delight.
For two months and two weeks, I lived (and loved) femininity. The instructors were all Pink Siders and very friendly. Very friendly, if you know what I mean.
I even got to suck Heather's big cock seven or eight times.
So, two-and-a-half months into my training, Heather declared me ready-for-prime-time.
Which meant I would be living full time as Jennifer.
What a relief!
The only problem could have been at school.
Maybe everyone there wasn't as tolerant as the people reading this story.
So I was nervous my first school day as Jennifer.
Mom helped me pick out my outfit (I didn't need cosmetic assistance any more). I wore black stockings and garters; black, four-inch-stiletto pumps; a black miniskirt; and a pink, silk top. Hot pink finger- and toenail polish. Hair, which had grown, styled nicely.
I looked hot!!
But a bit scared.
Daddy drove me to school. He and I had gotten up an hour early that morning to empty me so I could calm down.
He gave me a nice, chaste kiss and I opened the car door. I set one heeled foot and long leg out, then the other. People stopped and looked.
I stood up and closed the car door. People stopped and looked.
Nobody screamed, "Hey, fag, go home" or anything.
I walked into school. Stared at, but unmolested.
I took my seat in Mr. Chaucer's English class. Greg's seat, now Jennifer's.
And suddenly it dawned on the onlookers.
The new babe was the former Greg!
Oh1
That was news!
A low buzz in the class.
I heard a female voice say, "Pink-Sider."
I caught Tiffany's eye and she smiled.
Mr. Chaucer restored order, but he was giving me a nice staredown during much of the class.
Well.
So far so good, I thought.
Tiffany pointedly didn't walk with me as we changed classes. She said I needed to have space if I was to grow as a pantyboy.
Well. I did have some space.
The girls avoided me, of course.
The boys were divided. Some found me disgusting. Some wanted to push me into a dark corner, pull my panties down and fuck me. Some wanted to take me home and introduce me to their parents as their fiancée.
Then there was Mark Hardwood.
The young man whom Mom had predicted, would ask me to the senior prom.
Mark asked if he could sit with me at lunch. I blushed and allowed it.
I had known Mark a little as Greg. But being Jennifer made it all different.
"What's your name now, Greg?" Mark asked directly.
I looked at him shyly and said, "Jennifer."
He eased back and repeated it. "Jennifer. What a beautiful name."
I waited. And then he said it.
"It's perfect for someone as beautiful as you, Jennifer."
OK. An old line, but it was the first time I heard it as a girl.
Mark saw that he had hit the bullseye and he continued.
"You're the prettiest girl in school."
I blushed. Tiffany was pretty too, I thought. But maybe Mark was right. Why not?
"Thank you," I whispered with downcast eyes.
"Jennifer, could you and I go out? I mean to a movie or something? Maybe on Friday?"
Wow. Mark worked fast.
I pretended to think about it, but we both knew I would agree to a date.
As it turned out, it was good for Mark that he moved quickly, because that day I got seven other requests for a date. And 32 the rest of that week
It was fun being a girl!
You probably think that I got awfully randy waiting four days until Friday. Having only Daddy's sweet tickles to keep me empty.
In truth, I ran into Mark later that afternoon and asked if he would like to stop by my house after school that day for "cookies and milk."
His handsome face beamed with the delight a man feels when he knows he's about to get lucky.
And lucky Mark got.
I got home first and set out the cookies and milk. I called Mom and asked her not to disturb what was happening my bedroom when she got home. She gave me an enthusiastic, "You go, girl."
Mark rang the doorbell ten minutes later.
Oh, he was dishy!
And he wanted me.
True to my invitation, I took him into the kitchen and gave him cookies and milk. As I sat on his lap. And submitted to his hot, tonguey kisses. As he felt me up.
His head almost exploded when he discovered that I was wearing stockings and a garter belt. Not pantyhose.
And he loved feeling my stiffie through my panties as we kissed.
Oh dear. It was so exciting that I drenched my poor panties.
Which delighted us both.
Oh dear.
He took his cock out after that and I slipped to my knees between his legs.
His cock was delicious.
I know because I ate it for 32 minutes. And swallowed two major cums.
The post-fellatric kissing got us so steamed up that fucking had to be next.
So I led Mark to my bedroom and stripped to my bra, garters and stockings. While he stripped all the way.
I whispered instructions to him about the use of the bottle of Spermbutt Anal Lubricant on my night stand.
He kissed me and ignored all that. Choosing to engage in the fiercest analingus I had yet experienced.
It was astounding, girls. I saw new colors and visited strange realms.
And made a proper mess of my sheets. Twice.
While he fucked me, all I could think was, this is my life from now on.
A simpering little pansy-, nancy-, sissy-, pantyboy looking for handsome men who want to stick their big cocks up my bum.
I was a Pink Sider. A magnet for men. A source of pleasure and a receiver of pleasure.
Not bad, eh?
I highly recommend it.
Please tell me what you think at bc20002015@hotmail.com
My other stories on nifty:
"Stunners" transgender -- tv
"Acting Up" transgender -- control
"Panty Pleasures" transgender -- young friends
"Woodville" transgender -- tv
"Mothered" transgender -- control
"Panty Town" transgender -- teen
"Tradition" transgender -- teen
"Punished" transgender -- high school
"Panty Paradise" transgender -- teen
"Kevin and Molly Go to Camp" -- transgender -- teen
"Lovelife" -- transgender -- high school
"My Three Sissies" -- transgender -- tv
"Acting Out" -- transgender -- high school
"Explorers" -- transgender -- high school
"Pantied" -- transgender -- young friends
"Rebuilding" -- transgender -- teen
"The Au Pair" -- transgender -- surgery
"Birthday Girl" -- transgender -- teen
"Genes" -- transgender -- high school
"Brothers in Panties" -- transgender -- teen
"Coach" -- transgender -- control
"Intervention" -- transgender -- high school
"Winners" -- transgender -- teen
"Teased" transgender -- high school
"Irish Girls" transgender -- teen
"Finished" -- transgender -- teen
"Role Model" -- transgender -- high school
"Freedom" -- transgender -- high school
"Panty Fiesta" -- transgender -- control
"Experiments" -- transgender college
"One Fine Day" -- transgender -- teen
"Stiff Resistance" -- transgender -- teen
"Poker" -- transgender -- tv
"Panty Sabbatical" -- transgender -- high school
"Published" -- transgender -- tv
"Stripped" -- transgender -- high school
"Trained" -- transgender -- control
"Something Better" -- transgender - tv
"Fulfilled" -- transgender -- tv
"Private Matters" -- transgender -- high school
"Hard Times" -- transgender -- tv
"Girl Nights" -- transgender -- control
"Geography" -- transgender -- tv
"Somewhere" -- transgender -- high school
"Next Door Bride" -- transgender -- chemical (though I don't think it has
chemicals)
"Service" -- transgender -- tv
"Test Driven" -- transgender -- tv
"Sissy Stepmother" -- transgender -- tv
"Slacker Moms" -- transgender -- tv
"Sissies and the City" -- transgender -- tv
"Paid in Full" -- transgender -- tv
"Alternative Education" -- transgender -- control
"The Boy Bride" -- transgender -- high school
"Stiff Competition" -- transgender -- teen
"Reservations" -- transgender -- tv
"Panty Pride" -- transgender -- tv
"The Panty Life" -- transgender -- tv
"Super" -- transgender -- tv
"Stocking Boys" -- transgender -- tv
"Panty Secrets" -- transgender -- tv
"Auntie's New Panties" -- transgender -- tv
"Good Riddance" -- transgender -- tv
"Generations" -- transgender -- tv
"Fully Fashioned" -- transgender -- tv
"Tommy's Summer Job" -- transgender -- tv
"Tuition Assistance" -- transgender -- tv
"Sweeties" -- transgender -- young friends
"Pretty Boy" -- transgender -- high school
"Competition" -- transgender -- high school
"Strokes" -- transgender -- high school
"Hosed" -- transgender tv
"Sanctuary" -- transgender – tv
"Happily Married" – transgender – tv
"Late Vocation" – transgender – tv
"Kelly in Miniskirts" – transgender - tv
"Best Neighborhood Ever" – transgender - tv
"Chrissie Goes to College" – transgender - tv
"Corporate Incentives" – transgender - tv